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β-Cryptoxanthin

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(Redirected fromBeta-cryptoxanthin)
β-Cryptoxanthin[1]
Cryptoxanthin
Cryptoxanthin
Names
IUPAC name
(3R)-β,β-Caroten-3-ol
Systematic IUPAC name
(1R)-3,5,5-Trimethyl-4-[(3E,5E,7E,9E,11E,13E,15E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-ol
Other names
  • Cryptoxanthol
  • Caricaxanthin
  • (R)-all-trans-β-Caroten-3-ol
  • Hydroxy-β-carotene
  • kryptoxanthin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
E numberE161c(colours)
UNII
  • InChI=1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m1/s1 checkY
    Key: DMASLKHVQRHNES-FKKUPVFPSA-N checkY
  • InChI=1/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m1/s1
    Key: DMASLKHVQRHNES-FKKUPVFPBQ
  • O[C@@H]2C/C(=C(/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C1=C(\C)CCCC1(C)C)C)C)C)C)C(C)(C)C2)C
Properties
C40H56O
Molar mass552.85 g/mol
Melting point169 °C (336 °F; 442 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

β-Cryptoxanthin is a naturalcarotenoid pigment. It has been isolated from a variety of sources including the fruit of plants in the genusPhysalis, orange rind, winter squashes such as butternut, papaya, egg yolk, butter, apples, and bovine blood serum.[1]

Chemistry

[edit]

In terms of structure, β-cryptoxanthin is closely related toβ-carotene, with only the addition of ahydroxyl group. It is a member of the class of carotenoids known asxanthophylls.

In a pure form, β-cryptoxanthin is a red crystalline solid with a metallic luster. It is freely soluble inchloroform,benzene,pyridine, andcarbon disulfide.[1]

Biology and medicine

[edit]

In the human body, β-cryptoxanthin is converted tovitamin A (retinol) and is, therefore, considered aprovitamin A. As with other carotenoids, β-cryptoxanthin is an antioxidant and may help preventfree radical damage to cells and DNA, as well as stimulate the repair of oxidative damage to DNA.[2]

Recent findings of an inverse association between β-cryptoxanthin and lung cancer risk in several observational epidemiological studies suggest that β-cryptoxanthin could potentially act as a chemopreventive agent against lung cancer.[3] On the other hand, in the Grade IV histology group of adult patients diagnosed withmalignant glioma, moderate to high intake of β-cryptoxanthin (for secondtertile and for highest tertile compared to lowest tertile, in all cases) was associated with poorer survival.[4]

Other uses

[edit]

β-Cryptoxanthin is also used as a substance to colour food products (INS number 161c). It is not approved for use in the EU[5] or USA;[citation needed] however, it is approved for use in Australia and New Zealand.[6]

References

[edit]
  1. ^abcMerck Index, 11th Edition,2612.
  2. ^Lorenzo, Y.; Azqueta, A.; Luna, L.; Bonilla, F.; Dominguez, G.; Collins, A. R. (2008)."The carotenoid β-cryptoxanthin stimulates the repair of DNA oxidation damage in addition to acting as an antioxidant in human cells".Carcinogenesis.30 (2):308–314.doi:10.1093/carcin/bgn270.PMID 19056931.
  3. ^Lian, Fuzhi; Hu, Kang-Quan; Russell, Robert M.; Wang, Xiang-Dong (2006)."β-Cryptoxanthin suppresses the growth of immortalized human bronchial epithelial cells and non-small-cell lung cancer cells and up-regulates retinoic acid receptor b expression".International Journal of Cancer.119 (9):2084–2089.doi:10.1002/ijc.22111.PMID 16841329.
  4. ^Delorenze, Gerald N; McCoy, Lucie; Tsai, Ai-Lin; Quesenberry, Charles P; Rice, Terri; Il'yasova, Dora; Wrensch, Margaret (2010)."Daily intake of antioxidants in relation to survival among adult patients diagnosed with malignant glioma".BMC Cancer.10: 215.doi:10.1186/1471-2407-10-215.PMC 2880992.PMID 20482871.
  5. ^UK Food Standards Agency:"Current EU approved additives and their E Numbers". Retrieved2011-10-27.[permanent dead link]
  6. ^Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved2011-10-27.
Carotenes (C40)
Xanthophylls (C40)
Apocarotenoids (C<40)
Vitamin A retinoids (C20)
Retinoid drugs
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